5-hydroxy-L-tryptophan   Click here for help

GtoPdb Ligand ID: 4671

Synonyms: 5-hydroxytryptophan
PDB Ligand
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 4
Rotatable bonds 3
Topological polar surface area 99.34
Molecular weight 220.08
XLogP -1.68
No. Lipinski's rules broken 0
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Canonical SMILES OC(=O)C(Cc1c[nH]c2c1cc(O)cc2)N
Isomeric SMILES OC(=O)[C@H](Cc1c[nH]c2c1cc(O)cc2)N
InChI InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)/t9-/m0/s1
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
L-Aromatic amino-acid decarboxylase
L-Tryptophan hydroxylase 1
L-Tryptophan hydroxylase 2
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Proton-coupled Amino acid Transporter 1 Hs Inhibitor Inhibition 3.0 pKi - 2
pKi 3.0 (Ki 9x10-4 M) [2]
Proton-coupled Amino acid Transporter 2 Hs Inhibitor Inhibition 2.8 pIC50 - 1
pIC50 2.8 (IC50 1.6x10-3 M) [1]